EP4365172A1 - Heterocyclic compound and harmful-arthropod-controlling composition containing same - Google Patents

Heterocyclic compound and harmful-arthropod-controlling composition containing same Download PDF

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Publication number
EP4365172A1
EP4365172A1 EP22833161.7A EP22833161A EP4365172A1 EP 4365172 A1 EP4365172 A1 EP 4365172A1 EP 22833161 A EP22833161 A EP 22833161A EP 4365172 A1 EP4365172 A1 EP 4365172A1
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Prior art keywords
group
optionally substituted
compound
halogen atoms
chain hydrocarbon
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German (de)
English (en)
French (fr)
Inventor
Masayuki Tashiro
Shinichiro Murakami
Takayuki SHIODA
Hidemitsu MINEGISHI
Takamasa Tanabe
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to a heterocyclic compound and a composition for controlling harmful arthropods comprising the same.
  • Patent Document 1 NO 2006/044552
  • An object of the present invention is to provide a compound having an excellent efficacy for controlling harmful arthropods.
  • the present inventors have intensively studied to find compounds having an excellent efficacy for controlling harmful arthropods, and as a result, found that a compound represented by the below-mentioned formula (I) has an excellent efficacy for controlling harmful arthropods.
  • the present invention includes the followings.
  • the present invention can control harmful arthropods.
  • halogen atom represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • halogen atoms or the substituents may be identical to or different from each other.
  • CX-CY represents that the number of carbon atoms is from X to Y.
  • C1-C6 represents that the number of carbon atoms is from 1 to 6.
  • chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group.
  • alkenyl group examples include vinyl group, 1-propenyl group, 2-propenyl group. 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethy-l,1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group, and 5-hexenyl group.
  • alkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group, and 5-hexynyl group.
  • alkoxy group examples include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tert-butoxy group, pentyloxy group, and hexyloxy group.
  • alkenyloxy group examples include 2-propenyloxy group, 2-butenyloxy group, and 5-hexenyloxy group.
  • alkynyloxy group examples include 2-propynyloxy group, 2-butynyloxy group, and 5-hexynyloxy group.
  • alkylsulfanyl group examples include methylsulfanyl group, ethylsulfanyl group, isopropylsulfanyl group, and hexylsulfanyl group.
  • alkylsulfinyl group examples include methylsulfinyl group, ethylsulfinyl group, isopropylsulfinyl group, and hexylsulfinyl group.
  • alkylsulfonyl group examples include methylsulfonyl group, ethylsulfonyl group, isopropylsulfonyl group, and hexylsulfonyl group.
  • cycloalkyl group examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group.
  • cycloalkenyl group examples include cyclopropenyl group, cyclobufenyl group, cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group.
  • C6-C10 aryl group examples include phenyl group, indenyl group, indanyl group, naphthyl group, and tetrahydronaphthyl group.
  • Examples of the "three- to seven- membered nonaromatic heterocyclic group" include aziridinyl group, oxiranyl group, thiranyl group, azetidinyl group, oxetanyl group, thietanyl group, pyrrolidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, piperidyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, azepanyl group, oxepanyl group, thiepanyl group, pyrazolynyl group, pyrazolidinyl group, imidazolinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isoxazolinyl group
  • Examples of five- to ten- membered aromatic heterocyclic group include a five-membered aromatic heterocyclic group, a six-membered aromatic heterocyclic group, a nine-membered aromatic heterocyclic group, and a ten-membered aromatic heterocyclic group.
  • Examples of the five-membered aromatic heterocyclic group include pyrrolyl group, furyl group, thienyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, oxadiazolyl group, and thiadiazolyl group.
  • Examples of the six-membered aromatic heterocyclic group include pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group and tetrazinyl group.
  • Examples of the nine-membered aromatic heterocyclic group include indolyl group, indazolyl group, benzoimidazolyl group, imidazopyridyl group, benzothiophenyl group, and benzofuranyl group.
  • Examples of the ten-membered aromatic heterocyclic group include quinolyl group, isoquinolyl group, quinazolinyl group, and quinoxalinyl group.
  • phenyl C1-C3 alkyl group examples include benzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 4-(trifluoromethyl)benzyl group, and 2-[4-(trifluoromethyl)phenyl]ethyl group.
  • N-oxide of the compound represented by formula (I) examples include the compound represented by the following formula. [wherein the symbols are the same as defined above]
  • the present compound and the intermediate compound A may be existed as one or more stereoisomers.
  • the stereoisomer include enantiomer, diastereoisomer, and geometric isomer.
  • Each stereoisomer, and stereoisomer mixture(s) in an arbitrary ratio thereof are included in the present compound.
  • the present compound or its N-oxide, and the intermediate compound A may form acid addition salts.
  • the acid to form the acid addition salt include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid; and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid.
  • the acid addition salt may be obtained by mixing the present compound or its H-oxide, and the intermediate compound A with an acid.
  • Embodiments of the compound N of the present invention include the following compounds.
  • a compound represented by formula (I-2) (hereinafter, referred to as “compound (1-2)") can be prepared by reacting a compound represented by formula (I-1) (hereinafter, referred to as “compound (I-1)”) with a sulfurizing agent. [wherein the symbols are the same as defined above]
  • the reaction is usually carried out in a solvent or in the absence of a solvent.
  • the solvents include ethers (such as tetrahydrofuran (hereinafter, referred to as "THF”), 1,4-dioxane, 1,2-dimethoxyethane (hereinafter, referred to as "DME”),methyl tert-butyl ether (hereinafter, referred to as “MTBE”), diethyl ether) (hereinafter, collectively referred to as “ethers”); halogenated hydrocarbons (such as dichloromethane, chloroform) (hereinafter, collectively referred to as "halogenated hydrocarbons”); hydrocarbons (such as hexane, toluene, xylene) (hereinafter, collectively referred to as "hydrocarbons”); nitriles (such as acetonitrile) (hereinafter, collectively referred to as "nitriles”); organic bases (such as trie
  • sulfurizing agent examples include phosphorus pentasulfide, 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide (hereinafter, referred to as "Lawesson's reagent").
  • the sulfurizing agent is usually used within a range of 1 to 3 molar ratio(s) as opposed to 1 mole of the compound (1-1).
  • the reaction temperature in the reaction is usually within a range of 0 to 200°C.
  • the reaction period in the reaction is usually within a range of 1 to 24 hour(s),
  • a compound represented by formula (1-3) (hereinafter, referred to as “compound (I-3)” can be prepared by reacting a compound represented by formula (M-1) (hereinafter, referred to as “compound (M-1)” with a carbonylating agent. [wherein the symbols are the same as defined above]
  • the reaction is usually conducted in a solvent.
  • the solvents include ethers, halogenated hydrocarbons, hydrocarbons, and mixtures of these solvents.
  • carbonylating agent examples include phosgene, triphosgene, dimethyl carbonate, and carbonyl diimidazole (hereinafter, referred to as "CDI").
  • a base may be used in the reaction a needed.
  • the base include organic bases; alkali metal carbonates (such as sodium carbonate, potassium carbonate) (hereinafter, referred to as “alkali metal carbonates”); and alkali metal hydrides (such as sodium hydride) (hereinafter, referred to as “alkali metal hydrides”).
  • the carbonylating agent is usually used within a range of 1 to 2 molar ratio(s), as opposed to 1 mole of the compound (M-1).
  • the base When a base is used in the reaction, the base is usually used within a range of 2 to 4 molar ratios, as opposed to 1 mole of the compound (M-1).
  • the reaction temperature in the reaction is usually within a range of 0 to 120°C.
  • the reaction period in the reaction is usually within a range of 0.5 to 24 hours,
  • a compound represented by formula (1-4) (hereinafter, referred to as "compound (I-4)) can be prepared by reacting the compound (M-1) with a thiocarbonylating agent. [wherein the symbols are the same as defined above]
  • thiocarbonylatihg agent examples include thiophoagene.
  • the reaction can be conducted by using the thiocarbonylating agent in place of the carbonylating agent according to the process 2.
  • a compound represented by formula (1-5) (hereinafter, referred to as “compound (1-5)”) can be prepared by reacting a compound represented by formula (M-2) (hereinafter, referred to as “compound (M-2)” with a compound represented by formula (M-3) (hereinafter, referred to as “compound (M-3)”) in the presence of a base.
  • M-2 compound represented by formula (M-2)
  • M-3 compound represented by formula (M-3)
  • the reaction is usually conducted in a solvent.
  • the solvent include ethers; hydrocarbons; nitriles; apromatic polar solvents (such as dimethylformamide (hereinafter, referred to as “DMF”), N-methylpyrrolidone (hereinafter, referred to as “NMP”), dimethylsulfoxide (hereinafter, referred to as “DMSO”)) (hereinafter, collectively referred to as “apromatic polar solvents”); and mixtures of these solvents.
  • DMF dimethylformamide
  • NMP N-methylpyrrolidone
  • DMSO dimethylsulfoxide
  • bases examples include organic bases, alkali metal carbonates, and alkali metal hydrides.
  • the compound (M-3) is usually used within a range of 0.8 to 1.2 molar ratios, and the base is usually used within a range of 1 to 3 molar ratio(s), as, opposed to 1 mole of the compound (M-2).
  • a metallic catalyst may be used in the reaction as needed.
  • the metallic catalyst include copper catalysts (such as copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethane sulfonate benzene complex, tetrakis (acetonitrile)copper (I) hexafluorophosphate, and copper (I) 2-thiophenecarboxylate); nickel catalysts (such as bis(cyclooctadiene)nickel (0), nickel (II) chloride); palladium catalysts (such as palladium (II) acetate, tetrakis(triphenylphosphine) palladium (o), II), tris(dibenzylideneacetone)dipalladium (II)).
  • copper catalysts such as copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper
  • the metallic catalyst When the metallic catalyst is used in the reaction, the metallic catalyst is usually used within a range of 0.01 to 0.5 molar ratios as opposed to 1 mole of the compound (M-2).
  • a ligand may be used in the reaction as needed.
  • the ligand include triphenylphosphine, 4, 5-bis(diphenylphosphino)-9,9-dimethyl xanthene (hereinafter, referred to as "Xantphos"), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicylohexylphoshiho-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphoshino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphoshino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane
  • the ligand When a ligand is used in the reaction, the ligand is usually used within a range of 0.01 to 0.5 molar ratios, as opposed to 1 mole of the compound (K-2),
  • the reaction temperature of the reaction is usually within a range of -20 to 150°C.
  • the reaction period is usually within a range of 0.5 to 24 hours.
  • the Compound (M-2) is a commercially available compound, or can be prepared according to a known method.
  • N-oxide compound of the compound represented by formula (I) can be prepared by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be conducted according to the method described in U.S. 2018/0009778 A1 or WO 2016/121970 A1 .
  • a compound represented by formula (M-10) (hereinafter, referred to as “compound (M-10")) and a compound represented by formula (M-1S) (hereinafter, referred to as “compound (M-1S)) can be prepared according to the Scheme below.
  • X a represents a fluorine atom or a chlorine atom
  • Boc represents a t-butoacycarbonyl group
  • the other symbols are the same as defined above.
  • a compound represented by formula (M-4) (hereinafter, referred to as "compound (M-4)") can be prepared by using di-tert-butyl hydrazodicarboxylate in place of the compound. (M-3) according to the process 4.
  • a compound represented by formula (M-5) (hereinafter, referred to as “compound (M-5)”) can be prepared by reacting the compound (M-4) with an acid.
  • the reaction is usually conducted in a solvent.
  • the solvent include halogenated hydrocarbons, water, and mixture of these solvents.
  • Examples of the acid include mineral acids such as hydrochloric acid and sulfuric acid.
  • the acid is usually used within a range of 1 to 100 molar ratios as opposed to 1 mole of the compound (M-4).
  • the reaction temperature is usually within a range of 0 to 150°C.
  • the reaction period is usually within a range of 0.1 to 24 hours,
  • the compound (M-5) can be also prepared by reacting the compound (M-2) with hydrazine monohydrate.
  • the reaction is conducted in a solvent or in the absence of a solvent.
  • solvents include ethers; halogenated hydrocarbons; hydrocarbons; nitriles; nitrogen-containing aromatic compounds (such as pyridine) (hereinafter, referred to as "nitrogen-containing aromatic compounds”); aromatic polar solvents; and mixtures of these solvents.
  • the hydrazine monohydrate is usually used within a range of 1 to 10 molar ratios as opposed to a mole of the compound (M-2).
  • a base may be used in the reaction as needed.
  • the base include organic bases, alkali metal carbonates, and alkali metal hydrides.
  • the base is usually used within a range of 1 to 10 molar ratios as opposed to 1 mole of the compound (M-2).
  • the reaction temperature is usually within a range of -20 to 150°C.
  • the reaction period is usually within a range of 0.5 to 24 hours.
  • the compound (M-10) can be prepared by reacting the compound (M-5) with a compound (R-1) (hereinafter, referred to as "compound (R-1)" in the presence of a base.
  • the reaction is conducted in a solvent or in the absence of a solvent.
  • solvents include ethers, halogenated hydrocarbons, hydrocarbons, nitriles, nitrogen-containing aromatic compounds, aromatic polar solvents, and mixtures of these solvents.
  • bases examples include organic bases, alkali metal carbonates, and alkali metal hydrides.
  • the compound (R-1) is usually used within a range of 0.5 to 1.5 molar ratios, and the base is usually used within a range of 1 to 3 molar ratio(s), as opposed to 1 mole of the compound (M-5).
  • the reaction temperature is usually within a range of -20 to 150°C.
  • the reaction period is usually within a range of 0.5 to 24 hours.
  • the compound (R-1) is a commercially available compound or can be prepared according to known method.
  • the compound (M-10) can be prepared by reacting the compound (M-5) with a compound represented by formula (R-2) (hereinafter, referred to as "compound (R-2)") in the presence of a condensing agent and a base.
  • compound (R-2) a compound represented by formula (R-2)
  • the reaction is conducted in a solvent or in the absence of a solvent.
  • the solvent include ethers, halogenated hydrocarbons, hydrocarbons, nitriles, nitrogen-containing aromatic compounds, aromatic polar solvents, and mixtures of these solvents.
  • condensing agent examples include 1H-benzotriazol-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (hereinafter, referred to as "BOP"), N,N'-dicyclohexylcarbodiimide, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride.
  • Examples of the base include organic bases, alkali metal carbonates, and alkali metal hydrides.
  • the compound (R-2) is usually used within a range of 0,5 to 1.5 molar ratios, and the condensing agent is usually used within a range of 1 to 1.5 molar ratio(s), and the base is usually used within a range of 1 to 3 molar ratio (s), as opposed to 1 mole of the compound (M-5).
  • An additive agent may be used in the reaction as needed.
  • the additive agent include ethyl 2-cyano-2-(hydroxyamino)acetate, 1-hydroxybenzotriazole, and 1-hydroxy-T-aza-benzotrialzale.
  • the additive agent is usually used within a range of 0.1 to 0.5 molar ratios as opposed to 1 mole of the compound (M-5).
  • the reaction temperature is usually within a range of -20 to 150°C.
  • the reaction period is usually within a range of 0.5 to 24 hours.
  • the compound (R-2) is a commercially available compound, or can be prepared according to a known method.
  • the compound (M-1S) can be prepared by reacting the compound (M-10) with a sulfurizing agent.
  • the reaction can be conducted by using the compound (M-10) in place of the compound (I-1) according to the process 1.
  • the compound (M-10) can be prepared by reacting the compound (M-2) with a compound represented by formula (R-3) (hereinafter, referred to as "compound (R-3)”) in the presence of a base. [wherein the symbols are the same as defined above]
  • the reaction can be conducted by using the compound (R-3) in place of the compound (M-3) according to the process 4.
  • the compound (R-3) is a commercially available compound or can be prepared according to the known method.
  • a compound represented by formula (M-30) (hereinafter, referred to as “compound (M-30) ") and a compound represented by formula (M-3S) (hereinafter, referred to as “compound (M-3S)) can be prepared according to the following scheme. [wherein the symbols are the same as defined above]
  • the compound (M-30) can be prepared by reacting a compound represented by formula (R-3) (hereinafter, referred to as "compound (R-3)”) with a carbonylating agent.
  • the reaction can be conducted by using the compound (R-3) in place of the compound (M-1) according to the Process 2.
  • a compound (M-3S) can be prepared by reacting the compound (R-3) with a thiocarbonylating agent.
  • the reaction can be conducted using the compound (R-3) in place of the compound (M-1) according to the Process 3,
  • the compound (M-3S) can be also prepared by reacting the compound (M-30) with a sulfurizing agent.
  • the reaction can be conducted by using the compound (M-3O) in place of the compound (1-1) according to the Process 1.
  • the present compound can be mixed or combined with one or more ingredients selected from the group consisting of the following Group (a), Group (b), Group (c), and Group (d) (hereinafter, referred to as "present ingredient").
  • the mixing or combining represents that the present compound and the present ingredient are used concurrently, separately, or at an interval.
  • the present compound and the present ingredient may be incorporated as a separate formulation or one formulation.
  • composition A a composition comprising one or more ingredients selected from the group consisting of the Group (a), the Group (b), the Group (c), and the Group (d) (that is, the present ingredient), and the present compound (hereinafter, referred to as "Composition A").
  • the Group (a) is a group consisting of acetylcholinesterase inhibitors (for example, carbamate insecticides and organophosphate insecticides), GABA-gated chloride ion channel blockers, (for example, phenylpyrazole insecticides), sodium channel modulators (for example, pyrethroid, insecticides), nicotinic acetylcholine receptor antagonist modulators (for example, neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators (for example, macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mites growth regulators, mitochondrial ATP synthase inhibitors, uncouplers of oxidative phosphorylation, nicotinic acetylcholine receptor channel blockers (for example, nereistoxin insecticides),
  • the Group (b) is a group consisting of nucleic acid synthesis inhibitors (for example, phenylamide fungicides and acylamino acid fungicides), cytostatic and cytoskeletal inhibitors (for example, MBC fungicides), respiration inhibitors (for example, QoI fungicides and QiI fungicides), amino-acid synthesis and protein synthesis inhibitors (for example, anilinopyridine fungicides), signal-transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (for example, DMI fungicides such as triazoles), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducer, multisite fungicides, microbial fungicides, and other fungicidal ingredients. These agents are described in the classification based on the FRAC mode of action.
  • the Group (c) represents a group of plant growth modulating ingredients (including mycorrhizal fungus and rhizobia).
  • the Group (d) represents a group of repellent ingredients.
  • alanycarb + SX indicates a combination of alanycarb and SX.
  • SX means to any one of the present compounds selected from the compound classes SX1 to SX931.
  • any of the present ingredients as described below are a known ingredient, and can be obtained from a commercially available drug or can be prepared according to a known method.
  • the present ingredient represents a microorganism
  • the present ingredient can be obtained from a microorganism depositary authority.
  • the number in parentheses represents CAS RN (registered trademark).
  • SX milbemycin oxime + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine. + SX, nicotine-sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, oil of the seeds of Chenopodium anthelminticum + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phoaphamidon + SX, phosphine + SX, phox
  • Kurstaki strain EG2348 + SX Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp.. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp.
  • Amyloliquefaciens strain FZB24 + SX Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON/M/91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp.
  • a combination of the present ingredient in the above-mentioned Group (c) and the present compound 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymid
  • Examples of the ratio of the present compound to the present ingredient include, but are not particularly limited to 1000 : 1 to 1 : 1000, 500 : 1 to 1 : 500, 100 : 1 to 1 : 100, 50 : 1, 20 : 1, 10 : 1, 9 : 1, 8 : 1, 7 : 1, 6 : 1, 5 : 1, 4 : 1, 3 : 1, 2 : 1, 1 : 1, 1 : 2, 1 : 3, 1 : 4, 1 : 5, 1 : 6, 1 : 7, 1 : 8, 1 : 9, 1 : 10, 1 : 20, and 1 : 50 in the weight ratio (the present compound X: the present ingredient).
  • the present compound has control effect on harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.
  • harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.
  • harmful arthropods, harmful nematodes, and harmful mollusks include the followings.
  • Thysanoptera
  • Thysanura from the family Lepismatidae, for example, oriental silverfish (Ctenolepisma villosa) and moth fish (Lepisma saccharina); and the others.
  • Polydesmida from the family Paradoxosomatidae, for example, flat-backed millipede (Oxidus gracilis) and Nedyopus tambanus; and the others.
  • Isopoda from the family Armadillidiidae, common pill bug (Armadillidium vulgare); and the others.
  • the harmful arthropods such as harmful insects and harmful mites, harmful mollusks and harmful nematodes may be harmful insects and harmful mites, harmful mollusks and harmful nematodes which have a reduced susceptibility to or a developed resistance to an insecticide, a mitecide, a molluscicide or a nematicide.
  • the method for controlling harmful arthropods of the present invention is conducted by applying an effective amount of the Present compound or the Composition A to a harmful pest directly and/or a habitat where the harmful pest lives (for example, plant, soil, an interior of a house, and animal).
  • a method for controlling harmful arthropods of the present invention include foliar application, soil application, root application, shower application, smoking application, water-surface application, and seed application.
  • the Present compound or the Composition A is usually used by mixing it with inert carrier (s) such as solid carrier(s), liquid carrier(s), and gaseous carrier(s), surfactant(s), and the like, and as needed, adding thereto auxiliary agent(s) for formulation such as binder(s), dispersant(s), and stabilizer (s) to be formulated into an aqueous suspension formulation, an oily suspension formulation, an oil solution, an emulsifiable concentrate, an emulsion formulation, a microemulsion formulation, a microcapsule formulation, a wettable powder, a granular wettable powder, a dust formulation, a granule, a tablet, an aerosol formulation, a resin formulation, or the like.
  • inert carrier such as solid carrier(s), liquid carrier(s), and gaseous carrier(s), surfactant(s), and the like
  • auxiliary agent(s) for formulation such as binder(s), dispersant(s), and stabilizer (s) to be
  • the Present compound or the Composition A may be used by formulating it into a dosage form described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers- 271-276, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2Q16, ISSN:0259-2517.
  • These formulations usually comprise 0.0001 to 99% by weight ratio of the Present compound or the Composition A.
  • the solid carrier examples include fine powders and granules of clays (for example, pyrophyllite clay and kaolin clay), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid white clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride), and the others; as well as resins (for example, polyethylene, polypropylene, polyester, polyurethane, polyamide, and polyvinyl chloride).
  • clays for example, pyrophyllite clay and kaolin clay
  • talc calcium carbonate
  • diatomaceous earth zeolite
  • bentonite acid white clay, attapulgite, white carbon
  • ammonium sulfate vermiculite
  • perlite
  • liquid carrier examples include water, alcohols (for example, ethanol, cyclohexanol, benzyl alcohol, propylene glycol, and polyethylene glycol), ketones (for example, acetone and cyclohexanone), aromatic hydrocarbons (for example, xylene, phenyl xylyl ethane, and methylnaphthalene), aliphatic hydrocarbons (for example, hexane and cyclohexane), esters (for example, ethyl acetate, methyl oleate, and propylene carbonate), nitriles (for example, acetonitrile), ethers (for example, ethylene glycol dimethyl ether), amides (for example, N,N-dimethylformamide and N,N-dimethyloctanamide), sulfoxides (for example, dimethyl sulfoxide), lactams (for example, N-methylpyrrolidone and N-octyl
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.
  • surfactant examples include nonionic surfactants (for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters), and anionic surfactants (for example, alkyl sulfonates, alkyl aryl sulfonates, and alkyl sulfates).
  • nonionic surfactants for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters
  • anionic surfactants for example, alkyl sulfonates, alkyl aryl sulfonates, and alkyl sulfates.
  • the specific examples of the surfactant include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray M (registered trademark), and BANOLE (registered trademark).
  • Nimbus registered trademark
  • Assist registered trademark
  • Aureo registered trademark
  • Iharol registered trademark
  • auxiliary agent for formulation examples include binders, dispersants, colorants, and stabilizers, and the specific examples thereof include polysaccharides (for example, starch, gum arable, cellulose derivatives, and alginic acid), lignin derivatives, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids), acidic isopropyl phosphate, and dibutylhydroxytoluene.
  • polysaccharides for example, starch, gum arable, cellulose derivatives, and alginic acid
  • lignin derivatives for example, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids), acidic isopropyl phosphate, and dibutylhydroxytoluene.
  • examples of the plant include whole plant, stem and leaf, flower, ear, fruit, tree stem, branch, crown, seed, vegetative reproductive organ, and seedling.
  • a vegetative reproduction organ means a part of plant such as root, stem, and leaf which has a growth capability even when said part is separated from the plant body and placed into soil.
  • Examples of the vegetative reproduction organ include tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cuttihg. Stolon is also referred to as "runner”, and propagule is also referred to as "propagulum” and categorized into broad bud and bulbil.
  • Vine cutting means a shoot (collective term of leaf and stem) of sweet potato, glutinous yam, or the like.
  • Bulb corm or solid bulb, tuber, rhizome, cane cuttings, rhizophore, and tuberous, root are also collectively referred to as “bulb”.
  • cultivation of potato starts with planting a tuber into soil, and the tuber to be used is generally referred to as “seed potato”.
  • Examples of a method for controlling harmful arthropods by applying an effective amount of the Present compound or the Composition A to soils include a method of applying an effective amount of the Present compound or the Composition A to soils before planting plants or after planting plants, a method of applying an effective amount of the Present compound or the Composition A to a root part of a crop to be protected from damage such as ingestion by harmful arthropods, and a method of controlling harmful arthropods that ingest a plant by permeating and transferring an effective amount of the Present compound or the Composition A from a root into the interior of the plant body.
  • examples of the application method include planting hole treatment (spraying into planting holes, soil mixing after planting hole treatment), plant foot treatment (plant foot spraying, soil mixing after plant foot treatment, irrigation at plant foot, plant foot treatment at a later seeding raising stage), planting furrow treatment (planting furrow spraying, soil mixing after planting furrow treatment), planting row treatment (planting row spraying, soil mixing after planting row treatment, planting row spraying at a growing stage), planting row treatment at the time of sowing (planting row spraying at the time of sowing, soil mixing after planting row treatment at the time of sowing), broadcast treatment (overall soil surface spraying, soil mixing after broadcast treatment), side-article treatment, treatment of water surface (application to water surface, application to water surface after flooding), other soil spraying treatment (spraying of a granular formulation on leaves at a growing stage, spraying under a canopy or around a tree stem, spraying on the soil surface, mixing with surface soil, spraying into seed holes, spraying on the ground surfaces of furrows., spraying between plants), other irrigation treatment
  • Examples of the application to seeds include an application of the Present compound or the Composition A to seeds or vegetative reproductive organs, and specific examples thereof include spraying treatment in which a suspension of the Present compound or the Composition A is sprayed onto seed surface or the vegetative reproductive organ surface in the form of mist; smearing treatment in which the Present compound or the Composition A is coated a surface of seeds or the vegetative reproductive organ; a soaking treatment in Which the seeds are soaked into the solution of the Present compound or the Composition A for a certain time; and a method for coating the seeds or the vegetative reproductive organ with a carrier containing the Present compound or the Composition A (film coating treatment., pellet coating treatment).
  • Examples of the above-described vegetative reproductive organ include particularly seed potato.
  • the Composition A When the Composition A is applied to seeds or vegetative reproductive organs, the Composition A may be also applied to seeds or vegetative reproductive organs as a single formulation, or the Composition A may be applied to seeds or vegetative reproductive organs as multiple different formulations by multiple times.
  • Examples of the method in which the Composition A is applied as multiple different formulations by multiple times include, for exmaple, a method in which the formulations comprising as an active component the Present compound only are applied, and seeds or vegetative reproductive organs are air dried, followed by applying the formulations comprising the Present ingredient: and a method in which the formulations comprising as an active component the present compound and the Present ingredients are applied, and seeds or vegetative reproductive organs are air dried, followed by applying the formulations comprising the Present ingredients other than the already-applied Present ingredients, are included.
  • seeds or vegetative reproductive organs carrying the present compound or the Composition A means seeds or vegetative reproductive organs in the state where the present compound or the Composition A is adhered to a surface of the seeds or the vegetative reproductive organ.
  • the above-described seeds or vegetative reproductive organs carrying the present compound or the Composition A may be adhered by any other materials that are different from the present compound or the Composition A before or after being adhered the present compound or the Composition A to the seeds or vegetative reproductive organs.
  • the layer(s) is/are composed of one layer or a multiple layers. Also, when multiple layers are formed, each of the layer may be composed of a layer comprising one or more active ingredients, or a combination of a layer comprising one or more active ingredients and a layer not comprising an active ingredient.
  • Seeds or vegetative reproductive organs carrying the present compound or the Composition A can be obtained, for example, by applying the formulations comprising the present compound or the Composition A by the above-described application method to seeds to seeds or vegetative reproductive organs.
  • the application dose thereof is usually within a range of 1 to 10,000 g of the Present compound per 10,000 m 2 . In the case of being applied to seeds or vegetative reproductive organs, the dose of application dose thereof is usually within a range of 0.001 to 100 g of the Present compound per 1 Kg of seeds.
  • the Present compound or the Composition A is formulated into an emulsifiable concentrate, a wettable powder or a flowable etc., they are usually applied by diluting them with water so as to make an effective concentration of the active ingredients 0.01 to 10,000 ppm, and the dust formulation or the granular formulation, etc., is usually applied as itself without diluting them.
  • the resin preparation which is processed into a sheet or a string may be applied by winding a plant with a sheet or a string of the resin preparation, putting a string of the resin preparation around a crop so that the plant is surrounded by the string, or laying a sheet of the resin preparation on the soil surface near the root of a plant.
  • the application dose as an amount of the Present compound is usually within a range from 0.01 to 1,000 mg per 1 m 2 of an area to be treated, in the case of using it on a planar area. In the case of using it spatially, the application dose as an amount of the Present compound is usually within a range from 0.01 to 500 mg per 1 m of the space to be treated.
  • the Present compound or the Composition A is formulated into emulsifiable concentrates, wettable powders, flowables or the others, such formulations are usually applied after diluting it with water in such a way that a concentration of the active ingredient is within a range from 0.1 to 10,000 ppm. In the case of being formulated into oil solutions, aerosols, smoking agents, poison baits and the others, such formulations are used as itself without diluting it.
  • the composition of the present invention may be applied to the animals by a known method in the veterinary field. Specifically, when systemic control is intended, the composition of the present invention is administered to the animals as a tablet, a mixture with feed or a suppository, or by injection (including intramuscular, subcutaneous, intravenous and intraperitoneal injections).
  • the composition of the present invention is applied to the animals by means of spraying of the oil solution or aqueous solution, pour-on or spot-on treatment, or washing of the animal with a shampoo formulation, or by putting a collar or ear tag made of the resin formulations to the animal.
  • the dose of the compound of the Present compound is usually within a range from 0.1 to 1,000 mg per 1 log of an animal body weight.
  • composition of the Present compound or the Composition A may be used as an agent for controlling pests in agricultural lands such as paddy fields, fields, turfs, and orchards.
  • agricultural lands such as paddy fields, fields, turfs, and orchards.
  • plants include the followings.
  • the above plants are not specifically limited as long as they are generally cultivated cultivars.
  • the above plants also include plants which may be produced by natural breeding, plants which may be generated by mutation, F1 hybrid plants, and genetically modified crops.
  • the genetically modified crops include plants which have resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, or herbicide such as bromoxynil and dicamba; plants which can synthesize a selective toxin known in Bacillus app.
  • HPPD 4-hydroxyphenylpyruvate dioxygenase enzyme
  • ALS acetolactate synth
  • RNAi gene silencing
  • Me represents methyl group
  • Et represents ethyl group
  • Pr represents propyl group
  • i-Pr represents isopropyl group
  • t-Bu represents tert-butyl group
  • c-Pr represents cyclopropyl group
  • c-Bu represents cyclobutyl group
  • c-Pen represents cyclopentyl group
  • c-Hex represents cyclohexyl group
  • Ph represents phenyl group
  • Py2 represents 2-pyridyl group
  • Py3 represents 3-pyridyl group
  • Py4 represents 4-pyridyl group
  • Bn represents benzyl group.
  • substituent(s) When c-Pr, c-Bu, c-Pen, c-Hex, Ph, Py2, Py3, and Py4 has any substituent(s), the substituent(s) is described together with a substitution position before the symbol.
  • 1-CN-c-Pr represents 1-cyanocyclopropyl group
  • 3,4-F 2 -Ph represents 3,4-difluorophenyl group
  • 4-CF 3 -Py2 represents 4-(trifluoromethyl)-2-pyridyl group
  • 5-OCH 2 CF 2 CF-Py2 represents 5-(2,2,3,3,3-pentafluoropropoxy)-2-pyridyl group.
  • LCMS liquid chromatography / mass spectrometry analysis
  • IM represents an intermediate compound.
  • a compound represented by formula (A-3) wherein Q represents any substituents described in [Table A-3A] and [Table A-3B].
  • Triethylamine 1.75 mL was added to a mixture of the intermediate compound 9 1.10 g, THF 25 mL and triphosgene 1.04 g, and the resulting mixture was stirred at room temperature for 1 hour.
  • Aqueous saturated sodium hydrogencarbonate solution 20 mL was added to the resulting mixture, and the mixture was extracted with ethyl acetate.
  • the resulting mixture was dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • “Comp” represents "present compound”.
  • the present compound 31 700 mg was added to a mixture of iron powder 990 mg, ethanol 5 mL and acetic acid 0.29 mL at 90°C, and the mixture was stirred at 90°C for 5 hours.
  • the resulting mixture was filtered through Celite (registered trademark), and aqueous saturated sodium hydrocarbonate solution was added to the filtrates, and the mixture was extracted with ethyl acetate.
  • the resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the present compound 113 represented by the following formula 170 mg.
  • Acetyl chloride 0.03 mL was added to a mixture of the present compound 113 120 mg, triethylamine 0.06 mL, and chloroform 1 mL at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the present compound 115 represented by the following formula 120 mg.
  • substituent indicated in [Table L1] to [Table L3] hereinafter, referred to as "Compound class SXBS").
  • a 1 , A 2 , A 4 , and A 5 represent CH, and A 3 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX117").
  • a 1 , A 2 , A 4 , and A 5 represent CH, and
  • a 3 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX118").
  • a 3 represents C-F, A 1 , A 2 , and A 5 represent CH, and A 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX260").
  • a 3 represents C-1, A 1 , A 2 , and A 5 represent CH, and A 4 represents any one substituent indicated in [Table L13 to [Table L3] (hereinafter, referred to as "Compound class SX263").
  • a 2 represents C-F
  • a 1 , A 3 , and A 5 represent CH
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX284").
  • a 3 represents C-OCF 3
  • a 1 , A 2 , and A 5 represent CH
  • a 4 represents any one substituent indicated in [Table L1) to [Table L3] (hereinafter, referred to as "Compound class SX315").
  • a 2 represents C-I
  • a 1 , A 3 , and A 5 represent CH
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX383").
  • a 3 represents C-I, A 1 , A 2 , and A 5 represent CH, and
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX423").
  • a 2 represents C-Br, A 1 , A 3 , and A 5 represent CH, and A 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX446").
  • a 2 represents C-OCF 3 , A 1 , A 3 , and A 5 represent CH, and
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX451").
  • a 3 represents C-Me, A 1 , A 2 , and A 5 represent CH, and
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX456").
  • a 3 represents C-Cl, A 1 , A 2 , and A 5 represent CH, and
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX469").
  • a 3 represents C-CF 3 , A 1 , A 2 , and A 5 represent CH, and
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX474").
  • a 2 represents C-F, A 1 , A 3 , and A 5 represent CH, and A 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX508").
  • a 3 represents C-Br, A 1 , A 2 , and A 5 represent CH, and
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX518").
  • R 1c represents an ethyl group
  • a 2 represents C-Cl
  • a 1 , A 3 , and A 5 represent CH
  • a 4 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX525").
  • a 1 represents a nitrogen atom
  • a 2 , A 4 , and A 5 represent CH
  • a 3 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX603").
  • a 2 , A 4 , and A 5 represent CH, and A 3 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX605").
  • a 1 represents a nitrogen atom, A 3 , A 4 , and A 5 represent CH, and
  • a 2 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX636").
  • a present compound (L-2) wherein R 1b and R 1c represents a fluorine atom, and Q represents any one substituent indicated in [Table L4] to [Table L9] (hereinafter, referred to as "Compound class SX651").
  • a present compound (L-2) wherein R 1b and R 1c represents a chlorine atom, and Q represents any one substituent indicated in [Table L4] to [Table L9] (hereinafter, referred to as "Compound class SX652").
  • a present compound (L-2) wherein R 1b and R 1c represents a bromine atom, and Q represents any one substituent indicated in [Table L4] to [Table. L9] (hereinafter, referred to as "Compound class SX653").
  • a present compound (L-2) wherein R 1b and R 1c represents an ethyl group, and Q represents any one substituent indicated in [Table L4] to [Table L9] (hereinafter, referred to as "Compound class SX6S6").
  • a present compound (L-2) wherein R 1b and R 1c represents a propyl group, and Q represents any one substituent indicated in [Table L4] to [Table L9] (hereinafter, referred to as "Compound class SX657").
  • a present compound (L-2) wherein R 1b and R 1c represents an isopropyl group, and Q represents any one substituent indicated in [Table L4] to [Table L9] (hereinafter, referred to as "Compound class SX658").
  • a present compound (L-2) wherein R 1b and R 1c represents CF 3 , and Q represents any one substituent indicated in [Table L4] to [Table L9] (hereinafter, referred to as "Compound class SX660").
  • a 1 , A 3 , and A 4 represent CH, and A 5 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class SX705").
  • a 2 , A 3 , A 4 , and A 5 represent CH, and A 1 represents any one substituent indicated in [Table L1] to [Table L3] (hereinafter, referred to as "Compound class CX25").

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Insects & Arthropods (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP22833161.7A 2021-06-29 2022-06-28 Heterocyclic compound and harmful-arthropod-controlling composition containing same Pending EP4365172A1 (en)

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PCT/JP2022/025756 WO2023277014A1 (ja) 2021-06-29 2022-06-28 複素環化合物及びそれを含有する有害節足動物防除組成物

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JPH03236379A (ja) * 1989-12-25 1991-10-22 Sumitomo Chem Co Ltd オキサジアゾリノン誘導体、その製造法およびその殺虫剤としての用途
DE19531892A1 (de) * 1995-08-30 1997-03-06 Bayer Ag 1,3,4-Oxadiazolin-2-one
US20120041009A1 (en) * 2009-05-18 2012-02-16 Sumitomo Chemical Company, Limited Pyrimidine compound and its use in pest control
PL2967067T3 (pl) * 2013-03-15 2018-04-30 Monsanto Technology Llc N-,C-Dipodstawione azole do kontroli szkodników nicieniowych
CN109232550B (zh) * 2018-11-07 2021-08-06 青岛科技大学 一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物及其应用

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CN117561250A (zh) 2024-02-13

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